The name "American Eagle Airlines" was also used between April 1980 and April 1981 by an unrelated air charter service that suspended operations and filed bankruptcy before flying any scheduled operations.[4]

A Saab 340BPlus formerly operated by American Eagle at Los Angeles International Airport. (2007)

Envoy began as a collection of regional carriers with contracts to carry the American Eagle brand name. The first American Eagle flight was operated by Metroflight Airlines, which was a wholly owned subsidiary of Metro Airlines (formerly Houston Metro Airlines), on November 1, 1984, from Fayetteville, Arkansas to Dallas/Fort Worth International Airport. Metroflight utilized Convair 580 turboprop aircraft that had been formerly operated by Frontier Airlines. Other carriers that have flown in American Eagle (airline brand) livery include Executive Airlines, Command Airways, Air Virginia, Simmons Airlines, Chaparral Airlines and Wings West Airlines. Among other aircraft in its fleet, Chaparral flew Grumman I-C turboprops which were stretched, 37 passenger regional airliner versions of Grumman's successful propjet business aircraft and was one of only a few air carriers to ever operate the type in scheduled passenger service.

Until 1987 these third-party carriers flew under contract with American Airlines to provide regional feed to its hubs. During 1987 and 1988 AMR Corp. acquired its regional carriers, starting with Simmons Airlines. AMR's final airline d/b/a American Eagle acquisition was Executive Airlines in 1989.

By mid-1991 AMR had consolidated the number of carriers to four. The May 15, 1998, merger of Wings West and Flagship into Simmons (and the name change of Simmons Airlines to American Eagle Airlines) reduced the number of carriers flying as American Eagle under separate operating certificates to two: American Eagle Airlines, Inc. and Executive Airlines, Inc.

During 2007, AMR began studying ways to spin American Eagle Airlines off into a separate company, including, but not limited to, the possibilities of selling the company to either stockholders or to an unaffiliated third party. In 2008, AMR said any plans had been put on hold until the airline industry stabilized after the worldwide financial crisis. In July 2011, AMR announced the spin-off of American Eagle Airlines but those plans were again put on hold when Parent AMR Corp. filed for bankruptcy in November 2011. In 2014 the company changed its name to Envoy Air Inc.

Business Express was acquired by AMR Eagle Holdings Corporation in March 1999,[13] although it never flew under the American Eagle brand before being fully integrated into American Eagle Airlines, Inc. in December 2000.

For a brief period American Eagle Airlines cooperated with Trans World Airlines by allowing the placement of the TW two letter IATA code upon American Eagle Airlines flights feeding into Los Angeles and later New York's JFK Airports. These services were known as the Trans World Connection.[14][15]

These American Eagle Airlines/Trans World agreements were forged prior to and well in advance of AMR Corporation's route and asset acquisition of TWA in 2001.

Envoy operates from five hubs at Chicago-O'Hare, Dallas-Fort Worth, Miami, New York (at both Kennedy and LaGuardia airports). Former hubs include Boston, Nashville, San Jose, San Juan, Los Angeles, and Raleigh/Durham, with former focus cities being St. Louis and Washington. It was announced that the New York hub at both JFK and LaGuardia airports will close in May 2015.[16]

On January 14, 2014, American Airlines Group officially announced the rebranding of its American Eagle subsidiary as Envoy. Planes operated by American Eagle will continue to operate under the current American Eagle branding, but an "Operated by Envoy Air" label will be added, as is the case when contractors fly American Eagle aircraft.[20]

At October 2010, the average age of the Envoy Air fleet was 9.7 years.[25]

In September 2009, AMR Corporation announced plans to add a First Class cabin to its fleet of 25 Bombardier CRJ700 regional jets and also signed a letter of intent with Bombardier, Inc. to exercise options for the purchase of 22 additional CRJ700 SRS 702ER aircraft for delivery beginning in the middle of 2010.[26]

In January 2014, American Eagle's pilots union reached an agreement with the regional carrier's management that guarantees 60 of the new Embraer 175 aircraft that American Airlines ordered in December to be used with Eagle. The deal includes options for 90 other aircraft to be operated by the regional carrier. Delivery of the aircraft would begin in the first quarter of 2015. This deal was voted down by the pilots' union ALPA.

On May 8, 1987, American Eagle Flight 5452, operated by regional airline Executive Airlines, a CASA 212-200, was on a domestically scheduled passenger flight between San Juan, Puerto Rico-Mayaguez, Puerto Rico when it crashed short of Runway 09 while landing at Mayaguez. After impacting, the plane continued through a chain-link fence and a ditch. Of the six occupants onboard (four passengers and two crew), two were killed. The cause of the crash was determined to be improper maintenance in setting the flight idle propeller and engine fuel flow.

On May 9, 2004, American Eagle Flight 5401, an ATR-72, crashed in San Juan, Puerto Rico after the captain lost control of the aircraft while landing. Seventeen people were injured, but there were no fatalities.[31]

October 31, 1994: American Eagle Flight 4184, operated by AMR's regional airline Simmons Airlines (now American Eagle Airlines), an ATR 72, near Roselawn, Indiana. The aircraft inverted, dived, and crashed from a holding pattern at 10,000 feet (3050 m) "after a ridge of ice accreted beyond the deice boots" resulting in an unexpected aileron hinge moment reversal that subsequently resulted in the loss of control. The four crew and 64 passengers were all killed. In the months following the accident, American Eagle redeployed its ATR fleet to Miami and the Caribbean where icing is not an issue. The aircraft manufacturer, ATR, has since improved the anti-ice boots. The American Eagle aircraft were modified with the updated deicing system. All ATR 72s were retired from American Eagle's fleet in 2013.

July 9, 1995: American Eagle Flight 4127, an ATR 72 operated by Simmons Airlines, experienced a loss of the rear cabin entry door during its climb after taking off from O'Hare International Airport in Chicago. The cabin door opened shortly after the first officer began to pressurize the cabin; therefore, only a slight pressure differential existed between the cabin pressure and the atmospheric pressure. Lack of damage indicates the door was unlocked/unlatched when it opened. The airplane was one of fifteen aircraft equipped with a new handrail and door handle design which was different than the majority of the ATR 72 fleet. The old handle was pulled down to latch/lock the door and pushed up to unlatch/unlock the door. The direction of motion was reversed so that the handle was pushed up to latch/lock the door and pulled down to unlatch/unlock the door. A private citizen located the separated door in approximately two feet of water in the Des Plaines River on July 10, 1995. Following this incident, ATR designed another new door handle design which returns the handle motion to push up to unlatch/unlock, and pull down to latch/lock.[36]

January 2006: American Eagle Flight 3008 from San Luis Obispo to Los Angeles, a Saab 340B+, encountered icing at 11,000 feet and regained control only at 6,500 feet, after some 50 seconds' descent. During the incident, in which no one was injured, the autopilot disconnected, the stall alarm/clacker sounded, and the plane rolled sharply left and right, experienced vibration, and pitched down. Manual deice boots were activated and ice could be heard shedding off and striking the fuselage.[37][38] The NTSB report on this incident referenced three other Saab 340 icing incidents, as well as the Flight 4184 incident referenced above. The three were Nov. 11, 1998, in Eildon Weir, Victoria, Australia; June 28, 2002, in Bathurst, New South Wales, Australia; and June 18, 2004, in Albury, New South Wales, Australia.[39][40]